Every Lesson Worth Learning is Worth Revisiting

Gregory Ciotti |
October 29, 2015

Understanding is temporal and changes whenever you gain new information, experience, or shift your vantage point. To quote Heraclitus, “No man steps in the same river twice, for it's not the same river and he's not the same man.”

The daily grind often makes it difficult to look back on lessons learned in the workplace. Time is in short supply, but carving out a small block of it to reflect is important—the best people I’ve worked with frequently weigh the work they’re doing and the person they’re bringing to work.

After a particularly busy period at Help Scout, I found a few spare hours buried between the couch cushions. With thinking cap on and a contemplative pose in place, there were a few ideas I kept coming back to:

1. A little stress is a good thing.

The best kind of stress? Urgency. Feeling hurried is invigorating and drives you toward the finish line. You want to hold tight to a sense of haste without losing the headspace needed for strategy and forward thinking. After all, even the broadest shoulders can’t bear the burden of constant anxiety for long.

Ambitious deadlines help keep the pace. It’ll take some practice: enthusiasm too often makes for overly optimistic time estimates. As a rule, let your gut guide you to a date that “feels right,” then try to shorten it further.

As every writer knows, the most important ideas are prone to sit around idly, waiting to be conjured at the eleventh hour. Only a looming deadline can summon them.

2. Leadership isn’t just for appointed leaders.

Think of a time in your career when a project went sour. The response that stayed with you probably came from the person who made the first move, took ownership, and rallied everyone toward a better outcome.

Leadership in these cases doesn’t rest on roles and hierarchy, but on an ability to elevate the people around you. The late college basketball coach Jim Valvano described such a personality as “one of those people who, after you speak to them, you always feel better than before.” Even if the conversation is hard, even when discussing your current shortcomings or failings, you always leave with sights set high and the belief you can get it done.

Cherish the co-workers who care enough to push you; better yet, return the favor. Give the gift of encouragement, and never let pessimism drag down the spirits of those around you.

Truman Capote said it best: “Anyone who ever gave you confidence, you owe them a lot.”

3. You are the easiest person to fool.

It takes awareness to always share the unblemished truth, but you must keep stubborn standards: no one executes well without a firm grip on reality. Remember, it’s the seemingly innocuous, almost “positive” white lies (“Um, looks great!”) that most often sneak in and warp fact.

Some lies feel so small we actually say them out loud, unknowingly: “Yup, that’s all finished, I just need to…” Read: it’s not actually done, but we’ve convinced ourselves otherwise. A slight smudge of the truth feels insignificant, but with enough smudges, reality becomes a blur.

The first principle is that you must not fool yourself — and you are the easiest person to fool.

—Richard Feynman

4. Grade your work as a whole, not as an outcome.

Since the days of cave paintings, and probably before that, creative people have tried to judge their own work. One of the most famous examples of these efforts is Kurt Vonnegut’s letter grades given to his major pieces of writing:

After shaking off a fit of imposter syndrome, giving this a go myself led to a different realization—not once did I consider the execution, only the outcome. If there were bumps along the way, they didn’t make their way into my grading.

That’s a mistake; a positive outcome at any cost isn't realistic. For example, I recalled helping out on one of our job postings, and when I considered the result, I went with a confident “A.” But then I remembered how long it took and the slight confusion I created by revising a section that didn’t need revising. A minor misstep, but the room for improvement was obvious.

‘Better than before’ most often means improving execution and outcome, not one or the other.

5. A failure to communicate is your failure.

The job of communication is, in the words of author Neal Stephenson, “to condense fact from the vapor of nuance.” The burden of understanding is on you, not your audience.

“That’s not what I meant” is thus an admission of failure. To effectively share information is to be clear and captivating—in emails, in memos, in everything. Never assume attention is yours to keep without effort.

As a comedian on stage, you either kill, or you die. Harsh, right? But a small serving of angst will compel you to make points with a fierce exactness.

6. Feedback is an outcome-oriented activity.

I’ve always favored the term “necessarily honest” over “brutally honest,” because feedback is instructive language given to positively influence behavior. Feedback should be as blunt as it needs to be to incite change, and no more. Even brutally honest feedback is about being honest; it’s never about being brutal.

7. Energy + focus = productivity.

Period. Throw out every productivity app you have and learn to get a good night’s sleep instead. Then remove distractions. It really is that simple, but simple doesn’t mean easy. Although it’s been said many times in many different ways, author Maria Edgeworth penned my favorite variation: “If we take care of the minutes, the years will take care of themselves.”

8. Research should seek truth, not validation.

The purpose of learning—whether through research, debate, or any other means—is to arrive at the truth. But as illustrator Kris Straub demonstrates below, it’s an easy principle to champion but a hard one to live by.

After all, “strong opinions, weakly held” only becomes tricky at the weakly held part, especially when working with a team. Your own ideas, your favorite ideas, and the ideas you hope are correct frequently need to be cast aside for the greater good. Be willing to kill your darlings; finding the best possible solution depends on it.

We all have a tendency to use research as a drunkard uses a lamppost — for support, but not for illumination.

—David Ogilvy

9. Better judgement tends to show up late.

The worst regret is dealing with an eternity wrought from a hot-headed decision. H.G. Wells may have been asking too much when he said to wait for the common sense of the morning, but at the very least, have the patience to give it five minutes. What seems “right” in the heat of the moment often feels foolish once your good sense has had time to catch up.

Given the theme of rediscovery, I wonder what my opinion of these ideas will be in one year’s time. If I’m lucky, core tenets will crystallize and a few misconceptions will be discarded. Even if a handful of points are completely trashed, it’s better to have made the mistake than to keep making it.

Either way, a return trip will be its own reward. As author André Gide put it, “Everything's already been said, but since nobody was listening, we have to start again.”

About the author: Gregory Ciotti is on the Growth team at Help Scout, the invisible help desk that helps you build a company your customers love with more human, more helpful customer support tools.